Hydroxy-naphthalene-arylsulfoester azo dyestuff and process of making the same



-- 3:; by reduction Patented 10, 1928.

DELAWARE.

- UNITED STATES: PATENT OFFICE.

WILHELM NEEDMEIER, F LEVERKUSEN-ON-THE-RHINE, GERMANY, LSSIGNOR TO GRASSELLI DYESTUFF CORPORATION, OF NEW YORK, N. Y., A CORPORATION OF' nYnaoxY-NArnrnALENE-AnYLsULroEs'rER AZO DYESTUFF AND raocnss or MAKING THE same.

No Drawing. Griginal application filed July 21, 1926, Serial No. 124,089, and in Germany August 2, 19 24..

' Divided and this'application filed July 20, 1927. Serial No. 207,311.

I My invention consists in novel azo dyestuffs which contain as one ofthe compo nents dihydroxy-naphthalene with one of the hydroxy oups esterified 6 by an arlysulfonic acid an in processes of making thesame.

My invention provides for the production of very valuable orange to reddish-violet azo dyestuffs distinguished by clear shades 10 and excellent fastness to light and milling when applied to animal fibres.

' My preferred process for producing these novel azo dyestuffs consists in reacting ,in presence of a neutralizing agent with one molecular proportion of, an arylsultohal0 genid upon one molecular proportion of an azo dyestuff containing a dihydrexy-naph- .thalene compound, such as a dihydroxynaphthalene sulfonic acid, as one of its componentsr One of the hydroxyl groups of the latter is esterified by this process.

All the different dihydroxy-naphthalene compounds useful for the production of azo dyestuffs are applicable in my invention,

The arylsulfohalogenids can be typified by the most commonly technically used; i. e., p-

toluenesulfochloride, but .others such as be'n- -zenesulfochloride, or naphthalenesulfochlorides can be used to the same advantage in .30 my invention.

Y My novel dyestuifs are usually orange to reddish-violet owders. The are soluble in water and concentrated sul uric acid with from orange. to vviolet colors.

an aromatic amine and an amino-hydroxy-naphthaIene-sulfoarylester. l

-My' invention isiHustrated by the follow:

ing example: i Example-93 parts aniline are diazotized 40 in the usual manner and coupled in acetic acid solution with 278 parts 1-6-dihydroxynaphthalene-3-potassium sulfonate.

d estuif is isolated in the usualimanner and dissolved in 3000 parts water. 53 parts soda 5 ash and 190.5 parts p-toluenesulfochloride are added and the reaction mass heated to compounds They yield The.

7080 C. under stirring until the odor of the sulfochloride has disappeared. Most of the dyestufi' formed has separated and is isolated as usual. 1 It is in the dry state anorange-red powder, soluble in water and con-- centrated sulfuric acid with an orange-red color. It dyes wool from an acid bathorange-red shades of good fastness to light and milling. It has in the free state most probably therformula:

dew-O43,

and yields by reduction aniline and 5-amino- G-hydroxy-naphthalenc-l-p-toluolsulfocstcr- 3-sulfonic acid.

This is a divisionfof my coending application, Serial #124,089; filed uly 1, 1926. I ,claim As a new product the, mono-azo-dyestufls having in the free state" most probably the WILHELM NEELMEIER. 

